1258512-80-9Relevant articles and documents
Tetramic acids and derivatives by telluride-triggered dieckmann cyclizations
Dittmer, Donald C.,Avilov, Dmitry V.,Kandula, Venkata Subbarao,Purzycki, Matthew T.,Martens, Zachary J.,Hohn, Elliot B.,Bacler, Matthew W.
experimental part, p. 61 - 83 (2010/09/10)
Treatment of α-bromoacyl amides of esters of N-protected α-amino acids with lithium telluride yields an amide enolate which cyclizes to unstable tetramic acids (2, 4-pyrrolidinediones) which can be converted to stable derivatives (e.g. enol esters, silyl enol ethers, enol tosylates). Reaction conditions are modified to reduce unwanted side reactions: protonation of the enolate, selfcatalyzed intermolecular aldol rections of the tetramic acids, and potential racemization at the α-carbon atom of the amino acid.